Look. Don't do it. Really. What you want to learn: they're financed to the hilt, barely making ends meet, and living frivolously all for the sake of image... And you're doing it "the right way". You'll feel vindicated.

And if you learn that they are getting help from rich family (you won't, nobody ever admits that), you'll feel envious yet sanctimonious about not needing "help".

Maybe you'll learn that they made some smart investments.... Is that going to affect you investment strategy? You think any benefit will come from that? Nah, you'll probably just chalk it up to dumb luck.

Best case, you end up jealous, envious, or vindicated by the answer you get. Worst case, you offend them and you lose a friend.

Just assume whatever truth you would most prefer to believe, and worry about your own shit.

I just want to tell you that I was in a similar situation as you a few years ago. 6 years of no filings as a freelancer. "Reasons". With P&I I owed over $120k.

You're going to be ok. It's super scary. I spent years with terrible anxiety and fear about it. I felt really stupid and ashamed for putting myself in that situation, but it happened.

If you make decent money, you probably aren't eligible for Offer in Compromise — IRS, enrolled agent, and CPA all told me "nope, you make too much money for the IRS to budge." Even for P&I.

IANAL or CPA, and this isn't financial advice. Here's what I did:

0) My anecdotal experience is that the IRS officers on the PHONE lines are patient, helpful, empathetic and courteous. Maybe I got lucky. HOWEVER, brick-and-mortar IRS offices (and their employees) are basically the DMV, but a DMV where they can fuck your entire world up. I had horrible experiences going into the offices. Stick with the phones.

1) Get all your filings in. You literally can't do anything until all your filings are in. This is the first step.

2) Once they've received your filings, you'll start to get notices about how much you owe. There is going to be huge P&I, particularly if you didn't even file — the penalties and interest for not even filing are higher than filing and not paying. This is what burned me. My P&I was more than taxes owed. I would always call on the phone to talk through the bills with an IRS agent. They're not on your side, but they want you to pay... so they're happy to talk through it.

3) Save every piece of paper. Mail everything certified and keep your receipts from the post office. Get a good binder, with a tab for each year you're tracking. Every time you get a letter from the IRS related to that year, put it in the right file.

4) The IRS prioritizes years based on their own algorithm, it's not chronological. So if you are at risk for tax liens, you'll need to pay off the highest priority years first. You can "assign" payments to particular years. Do this ASAP to get them off your back for years they are collecting on hard. Call them and ask an agent. They would never say which one's were NOT at risk of collection activity, but they would always tell me which ones WERE. You can fill in the gaps.

5) You can't get put on a payment plan until your gross $ owed is below a certain number. I can't remember what it is. $80k? $50k? Sorry can't remember. You have to do everything you can to get below that number. I got ridiculously lucky and found out serendipitously there was an investment from a relative in my name which if I sold it would be enough to get me below the threshold. I sold it. It was supposed to be for my family some day.

6) Once you're below the threshold, you can start a payment plan. I think it's max 72 months. You tell them what you can pay, with the max time allowed at 72 months. Make sure you can pay it. If you miss a payment, you're fucked — they call to collect the entire lump sump and nullify the payment plan. Do not let that happen. I could afford $800/month. You can setup autopay with the IRS.

7) When you can afford lump sums, do it. The P&I continues to accrue DAILY during the payment plan, so every day that goes by you're getting fucked.

8) Depending on what state you're in (I was in California) you might want to consider paying the state first. Consult your tax professional. In California, the Franchise Tax Board does NOT fuck around and they have zero patience. The FTP put liens on me, froze my bank account, etc. The CPA who helped me get started said "The IRS is way more patient than the FTB — the FTB will ruin your world for pennies, pay them."

It sucks. It's expensive. There's excuses but nobody to blame but #1, so that makes it emotionally worse, at least it did for me.

Three years ago I joined a new company and got a big signing bonus, and as soon as the check cleared I logged into the IRS website and paid off my last $30k. I was overwhelmed, started crying like a baby. Glad I was alone. It was the end of one of the worst eras of my life.

Now I don't have to turn off the radio when those "Do you owe the IRS?" commercials come on... in fact now I smile, because it reminds me that I'm past it.

You will smile when they come on some day too. Stay strong and patient.

Use the IRS W-4 Withholding Calculator. It will tell you exactly what to put on your W-4. If you don't want to go through that, checking "married but withhold as single" should suffice, but there's a chance you will overwithhold. If you want to be sure, run through the calculator.

Started my career at a small company with the ultimate relaxed small office atmosphere. It was truly great. Great people, great atmosphere, great flexibility, etc. We were like a family. The only issue was that I was massively under-paid for the work and level of influence I had in the company. And it wasn't because the company wasn't willing to give raises, I too doubled my income over the nearly 9 years I stayed at that job, but I just wasn't where I needed to be and what the market was willing to pay. Throughout my years, money was the only thing that seemed imperfect.

After 9 years I tested the waters and wound up with a job offer. It wasn't a life-changing offer, but it was a solid offer, sounds similar to yours. It was maybe a 20% bump in pay with competitive benefits, but everything else about the prospect of leaving was terrifying. I'd be leaving the only job I ever knew, and leaving a team that felt like a family for a much more "corporate-y" place with many many more employees.

Despite a lot of hesitation and doubt, I stuck to my guns and turned in my resignation on good terms, and accepted the offer.

The first couple weeks at the new job were rough. I doubted everything. The environment was completely different, there were more rules, more processes, more management, etc. It didn't help that the owner of the company I left literally told me "you're making a huge mistake" and the person I worked closest with day-to-day at the old job warned me a million times that I'd hate the corporate environment and there's no way it makes sense to give up the flexible small office for money.

But...time passed. Everything quickly became more comfortable. The people and the processes and the work weren't worse, it was just different. It took me only a matter of weeks to stop doubting myself and to start thriving. After my first year at the new job, I would say without a doubt that I enjoyed coming to work just as much as I did at the old job.

Now that I've had several years of experience after leaving that first job, I can say without a doubt that the first job, while a great experience, wasn't really that unique. It was just a job. What was great was simply what I made of it, and that's sort of the point. If you're the kind of person who makes the most out of almost any situation, it's going to be difficult to go wrong. Most jobs are just jobs, neither objectively bad or good in an absolute sense, just different in their details.

Don't get me wrong, I'm certain there are some specific positions at specific companies with specific teams that are toxic and should be pretty much universally avoided, but that sort of thing can generally be sniffed out ahead of time. Obviously I wouldn't advocate anyone to take a job that they're uncomfortable with based on actual details of the job or observed evidence of toxicity, but if you have no logical reason to suspect that the new job will be worse than the old one, what are you worried about? There's a really high chance that it will be nothing more than different. And different in the sort of way that allows you to achieve your life goals faster and get ahead financially.

I really internalized the lesson with that experience that getting comfortable is career suicide. It hurt me to realize how behind the curve I was. Leaving that first job was a nice pay bump, but I was determined that even in the new job I wouldn't settle for just being comfortable. I was going to be a strong advocate for myself.

So at that second job, I thrived, and I felt that I had a very compelling case to make for a promotion, but things just weren't happening as quickly as I'd like. So this time, rather than waiting 9 years, I immediately went out and tested the waters again. By taking that second job I was much more marketable with the experience I gained, and if they weren't going to see that, maybe somebody else would.

So after 9 years at my first job, and not even quite a year and a half at my second job... I accepted an offer for my third job and again resigned on good terms. This time the financial gain was life changing. Compared to the salary I was making when I left that first job, in a year and I half I landed a 250%+ raise. And guess what? That third job is still... just a job. I once again adapted quickly, built relationships quickly, and enjoy this work just as much as anything else.

The point of all this rambling is simply: things are what you make of them for the most part. There are certain obvious red flags to look out for, but if you're the kind of person who can make the most of things, changing jobs shouldn't be as scary as you're making it out to be. I completely understand the power of getting very comfortable at a job, and how terrifying it is to "give it up", but you're not really giving anything up. You're just changing jobs. The new job will have coworkers, bosses, paychecks, benefits, vacations, etc. It will just be different. Use your brain to decide objectively if the new job is right for you, and if it sounds like a good fit, just set your mind on making it so and it most likely will be.

The guy is potentially defrauding a public school. Report it. Do the right thing.

I feel like I’m in the twilight zone right now. A lot of other comments are advocating doing nothing too. Is this how y’all run your own businesses? Just because he’s an hourly worker at a low wage doesn’t mean he’s not compelled to do right by himself and his employer.

Unbelievable honestly. From a personal finance perspective, this incident could result in OP moving up in the organization because he saw an issue and got it corrected. But your advice is to ignore it. Horrible advice on the whole.

That’s brutal man. I’m going through a rough breakup and got pretty drunk this Sunday after the oscars. When I was leaving the bar my Uber pulled up. A few minutes later it pulled up to a bank and the guy pulled a gun on me. Turns out it wasn’t my Uber at all the guy was just pulled up at the bar and said yes when I asked him if he was waiting for me. He had another guy in the car walk me up to the ATM where he made me max out my credit card that I had on me. I took out 4500 in cash advances. Then they made me disable the lost iPhone portion of my phone. I was stranded 20 miles from my apartment without a phone with vomit on my pants (partly from being that drunk, partly from fear).

People suck. Life is shitty sometimes. But we both survived. We both are now stronger and better prepared. I also am now over my ex because there honestly is much more important shit in the world lol.

You can just put $1 or some ridiculously low amount that the input will accept When asked about it later, I'll just up front say I don't make it a practice of setting salary expectation until I know the role and benefits better. You still end up in the ongoing dance back and forth eventually, but at least it gets you past the computer form and you're negotiating with a real person at that point.

Edit: love all the discussion on this - negotiating is a game I love to play and chat about. Lots of folks posting how this might get your resume auto filtered into oblivion. While that's true, my assumption was that if you're going through the numbers game of online automatic applications, you're already dicing with the algorithm gods anyway, and this just moves the game one step further without too much investment. If you really are hunting the dream job, I think there is no substitute for getting creative to get around these digital gate keepers and talking to a real person. Go to meetups the company hosts, offer to buy someone that works there a coffee or lunch even to ask about the work (not directly for a job), volunteer to help out with a project or even charity event the company is hosting. Hiring people want to find good candidates with minimal fuss, make it easy on them if you can - Good hunting y'all!

If you had 100 dollars and you "spent" it to get the company match, your 401k would have 200 bucks in it, a 100% ROI. If you instead spent that money on paying down your debt at 6%, you would save 50c for that month (the 6 bucks a year that 100 dollars loaned costs in interest/12 months). See how much less of an impact that 100 bucks has paying your debt faster when you could have instead put it towards your 401k?

On top of that instant difference in value, your 401k will grow in value. Even if the APR on your loans was much higher than 6%, you'd still be far better off investing that extra money (up to the match amount). Once you go past the match amount, the investment is only worth the market gains. At that point, you have to decide if you think your money will have a growth rate in the market bigger than your debts.

This argument of course, is applicable if you want to be mathematically optimal. This doesn't account for personal risk tolerance or your savings goals and so on. But it is why the prime directive has you invest up to company match first before dealing with paying more towards your debt (you still should ensrue you can pay your debt minimums first of course or else you'll suffer worse penalties/consequences).

Most of my career growth took place at my previous company, where I received a total of two promotions and one lateral transfer over three years.

My advice to you if you want to acheive that goal is this:

Be willing to move. The more willing you are to relocate, the more opportunities come available to you. Two of my three job changes involved moving more than 750 miles away.

Try to find a middle tier company in your industry that is growing. The more growth, the better. As the company grows and expands, more high-level positions open up for you to move into. My previous company doubled the size of its operation while I was there, so it's no wonder I was able to move up quickly.

Always be on the lookout for new jobs in your industry. Even if you just started a new job and you're required to stay there for one year (or forfeit your sign on bonus or relocation payment, for example), at least be aware of what positions are opening up in your industry regularly. It might give you an idea of what positions tend to be in higher demand.

Apply and interview for any jobs you're qualified for, even if you don't really want them. Initially I wasn't too interested in the open position at my current company because it was a step back title-wise (but a step up company-wise). A friend convinced me to apply and interview anyway. I ended up really liking what they had to offer, and accepted it. On the other hand, I once applied for a job didn't really want at a smaller company. They offered me the job, but I turned it down. Good thing too - they're now defunct. So make it a point to step outside your comfort zone - you never know what you might find.

Make sure you custom tailor your cover letter and resume to each position for which you're applying. Sending out copies of the same resume might not be properly representing your skills for that specific position.

300k is a pretty big goal! No reason you can't hit it though with the right skills and ability to market yourself. Good luck!

I'm not a lawyer, but I've been through some of this before. There are two critically important things for you to look in to, I think:

Have a lawyer certify/notarize the will in the presence of your grandmother, even if you can't hire one to re-write the will in a more ironclad way. You won't know if the uncles are going to fight until she dies. Hell, do they even know they're written out of the will yet? An officer of the court vouching for your grandmother's wishes will help quite a lot.

Get access to enough of her assets now to handle things like your travel, legal costs, final expenses, and home cleaning / staging during the sales process. There are a couple of ways you can do this. First, see if she'd be willing to open a home equity line of credit that lists you as a secondary borrower. This would be free to open, comes with a debit card, and you don't pay interest until you draw from the line of credit, which you would only do in the event of her death. You can also use the loan to pay the interest on the loan, so it would have no out of pocket cost for you. A bit more involved option is to pay a lawyer $1500 or so up front to set up a living trust with you as a co trustee, and have her assign all of her assets including the house to the trust. This can cut down dramatically or eliminate entirely the probate process by which the house would transfer ownership. A trustee can sell a house the trust controls at any time she wishes, estate beneficiaries can not sell a house until the title has been transferred by a lengthy probate process (which will be delayed even further if the uncles fight).

ETA: The reason this is better than just opening up a credit card is that having a way to pay expenses directly from the estate, is far, far better than paying expenses yourself and hoping you eventually get reimbursed by the estate.

If you get their rewards credit card, you get 3.59% on up to $15k w/ $500/mo spending.

You can get 4.59% on up to $20K w/ $1K/mo spending on their credit card. That's a little over $900/year. Its a few hoops, but it's worth it to me for months when I'm not churning on some new credit card (and even then I can easily get the 3.09% on 10K).

I am surprised no one has recommended this yet, but one of you could start working in the public domain (i.e. government jobs). The extent of that student loan is large enough to merit it. If you work in the public domain lets say as a High School Teacher for 10 years your loan will be forgiven.

No more eating out at bars and restaurants. Cheap meals everyday and learn to cook.

No more international vacations on a loan... Come on now. If you need to take a trip, set up a cheap budget and drive over to the next large city or something.

Gambling? Stop that now.

No more expensive shopping trips either. Go to Dillards and they'll have plenty of stuff for sale. I get all my work clothes from there and I pay something like $30-$40 for pants. They always seem to have a decent sale for last seasons clothes. 50% off plus an additional 30% off or something similar.

Now for your CC debt

Make a list of your CC debt. List interest rate and amount owed. Pay off whatever has the highest interest rate. I'd personally focus on paying off one at a time while paying the minimum on the others.

THE MOST IMPORTANT PART

BUDGET

you need to learn how to budget. Go search on google, there are plenty of resources. I'd personally make a spreadsheet with your income and expenses. See how much you can save and then calculate how much you can start putting towards CC debt. Making a budget isn't an overnight job. It can take a couple months of tweaking to get it right so no need to rush to perfect it.

For your Finance

Your fiance chose to be with you. You need to both sit down and talk about what you're going through. Explain to her that you made mistakes and need help working through it. Don't hide it from her. Be upfront about your position but at the same time I wouldn't go to her empty handed. I'd work on a plan to get out of debt and present it to her. More importantly, I'd ask her for her input. This would help her understand the situation as well as the lifestyle change. Either way, it's great that you're realizing this mistake now more than later. Imagine if you were married with kids, late 30's and you're still living paycheck to paycheck... It could be much worse and you make enough to cover the debt anyways, so it's not too bad.

As for running away

You could run away if you want. It doesn't mean that it'll fix your problems. What makes you think that you'd change your habits overnight if you started over? You're in a great position right now to make a great change in your life. You're also with the love of your life. Why leave that behind for whatever you might think is better on the other side. (BTW it's never better on the other side, it just looks like it)

Glad you asked! If you are a disciplined DIYer with a solid track record and the ability to keep emotions out of the picture, then you are going to be just fine on your own. People pay me for: financial planning (which covers budgeting, risk management, large expense planning, retirement planning, estate planning...and any specific issues), determining and constantly reviewing appropriate allocation (both for assets I manage and assets held outside like in a 401k, everyhting needs to work together), portfolio construction and monitoring (we are good at this, but this is not the largest benefit), discipline in tough market conditions, and making adjustments over time as your situation changes. If you are well organized (know where everything is, how it's invested, and why it's invested like it is), disciplined (won't make changes to a strategy when the markets move against you), and understand the amount of risk you currently are taking vs the purpose of the investment (if the need is close, don't take high risk, if you have lots of time, take as much risk as you either need or are comfortable with), then you should be just fine without me. Most people need someone to manage all of that - they simply are not equipped or don't have the time and energy. Vanguard did a study that determined that using an advisor adds about 3% annually to the long-term results, mostly based on the discipline and advising on an appropriate, well diversified allocation. Note that this isn't year-in year-out. I never say I'll outperform you, because I'm not the best investment picker of all time, but I'll make damn sure your money is invested with the least amount of risk needed to do the job it has to do and will do everything I can to make sure the specific investments are as rock solid as I can.